Water → HCID 59370342, compound

HRID 448904Notes

Reaction equation

HRID 448904 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[CH3:9])=[O:7])=[CH:4][C:3]=1[C:20]1[CH:21]=[N:22][C:23]([C:26]#[N:27])=[CH:24][CH:25]=1.C([O-])([O-])=[O:29].[K+].[K+].CCOC(C)=O.O>C1COCC1.[Li+].[OH-]>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6](=[O:7])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[CH3:9])=[CH:4][C:3]=1[C:20]1[CH:25]=[CH:24][C:23]([C:26]([NH2:27])=[O:29])=[N:22][CH:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 86642575HCID 86642575, compound

Product 1

HCID 59370342HCID 59370342, compound

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-3-(6-cyano-pyridin-3-yl)-N-(2-methoxy-phenyl)-N-methyl-benzamide 2-2 (29 mg, 0.077 mmol) in THF (0.5 mL), 1N LiOH (0.5 mL) and K2CO3 (10 mg, 0.073 mmol) were added. After stirring for 48 hrs at room temperature, EtOAc and water were added. The aqueous layer was removed and the organic layer was concentrated, dissolved in MeOH and subjected to preparative LCMS to yield 5-{2-chloro-5-[(2-methoxy-phenyl)-methyl-carbamoyl]-phenyl}-pyridine-2-carboxylic acid amide 24-1. MS (M+H)+: 396.0, tR=5.93 min (method 2).

Workup

  1. customThe aqueous layer was removed
  2. concentrationthe organic layer was concentrated
  3. dissolutiondissolved in MeOH

Sources & evidence

ORD record
ord-03e497504a64401cae61cb8bbc5afe89
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Reaction notes

Loading…